Patent GB-973236-A (GB)
Title: Improvements in or relating to the treatment of seeds
IPC: C07D277/74
Filed: 1962-05-04
Abstract: Isopropyl-ammonium-N-isopropyl- and furfuryl-ammonium-N-furfuryl-dithiocarbamate are prepared by reacting isopropyl or furfuryl amine with carbon disulphide. N-(3-chlorophenyl) tetrahydrophthalimide is prepared by reacting tetrahydrophthalic anhydride with 3-chloroaniline, in molar proportions, at temperatures up to 135 DEG C.  N-(3-chlorophenyl) pyruvamide is prepared by reacting 0.14 mole of 3, 31-dichlorophenyl -phosphazo-anilide with 0.3 mole of pyruvic acid, in toluene at 70 DEG C.  N-(3-chlorophenyl) tribromo-acetamide is prepared by reacting 0.06 mole of 3, 31-dichlorophenyl-phosphazo-anilide with 0.13 mole of tribromoacetic acid, in toluene at 90 DEG C.  N-(3-chlorophenyl) -4-amino-2-hydroxybenzamide is prepared by reacting 0.09 mole of 3, 31-dichlorophenyl-phosphazo-anilide with 0.195 mole of 4-amino-salicyclic acid, in toluene at reflux temperature. N-(4-chlorophenyl) a -chloropropionamide is prepared by reacting one mole of 4, 41-dichloro-phosphazo-anilide with two moles of a -chloropropionic acid, in toluene at reflux temperature. N, N1-bis (3, 4-dichlorobenzylidene)-3, 4, dichlorobenzylidene-diamine or tri-m, p-dichlorohydrobenzamide is prepared by reacting 3, 4-dichlorobenzaldehyde with ammonium hydroxide in methanol.  2, 4-dichloro-9-xanthenone is prepared by reacting one mole of 2-chlorobenzoic acid with one mole of 2, 4-dichlorophenol in a methanolic solution of sodium methoxide.  1, 3-bis (3-chloro-4-methylphenyl) thiourea is prepared by reacting 0.4 mole of 3-chloro-4-methyl-aniline with 0.2 mole of carbon disulphide in methanol at reflux temperature. a -chloro-a -(2, 4-dichlorophenyl) acetic acid is prepared by chlorinating 2, 4-dichloromandelonitrile with thionyl chloride and then hydrolyzing the product with aqueous sodium hydroxide. 2-benzothiazolyl N-(3-chlorophenyl) thiocarbamate is prepared by reacting one mole of mercaptobenzothiazol with one mole of 3-chlorophenyl isocyanate, and a catalytic amount of pyridine, in benzene at reflux temperature.  3-bromopropyl N-(4-bromophenyl) carbamate is prepared by reacting one mole of 3-bromo-1-propanol with one mole of 4-bromophenyl isocyanate and a catalytic amount of pyridine, in benzene at reflux temperature. 2-bromoethyl N-(4-bromophenyl) carbamate is prepared by reacting one mole of 2-bromoethanol with one mole of 4-bromophenyl isocyanate and a catalytic amount of pyridine, in benzene at reflux temperature. b -morpholino-p-bromopropiophenone hydrochloride is prepared by Mannich reaction of p-bromoacetophenone, formaldehyde and morpholine hydrochloride in acedic ethanol, at reflux temperature. Carboxymethyl N, N-dimethyl-dithiocarbamate is prepared by reacting chloroacetic acid with the sodium salt of N, N-dimethyl-dithiocarbamic acid.  The above compounds are used as antagonistic agents for treating seeds (see Division A2). Specifications 862,194 and 894,614 are referred to.ALSO:To counteract, nullify or reduce injurious effects, such as inhibition of bud and leaf growth and changes in leaf colour, produced on young plants when they are treated with a selective herbicide, such as isopropyl-N-phenyl, isopropyl-N-(3-chlorophenyl), 2,3,-dichloroallyl-N-propylthio, 2-(2, 4 - chlorophenoxycarbonyl) - 1 - methyl-ethyl-N-(3-chlorophenyl), n-propyl-N, N-dipropylthio or 4-chloro-2-butenyl-N-(3-chlorophenyl) carbamate, their seeds, before being planted, are treated with an antagonistic agent. Preferred antagonistic agents for counteracting the injurious effects of the selective herbicide 4-chloro-2-butenyl N-(-chlorophenyl) carbamate are: 41-chloro-2-hydroxyiminoacetanilide, 31, 41-dichloro - 2 - hydroxyiminoacetanilide, N-methyl-2, 5-dichlorobenzene sulphonamide, 2,4-dichloro-9-xanthenone, 5-(2,4-dichlorophenyl) hydantoin and isopropylammonium N-isopropyldithiocarbamate.  Other antagonistic agents are: 31-chloro-2-hydroxyiminoacetanilide, N-methyl-3,4-dichlorobenzenesulphonamide, p-toluene sulphonamide, 5-(3,4-dichlorophenyl), 5-(2-chlorophenyl) and 5-(4-chlorophenyl) hydantoin, piperidinium piperidine-1-carbodithioate, furfurylammonium-N-furfuryldithiocarbamate, isobutyl - ammonium - N - isobutyldithiocarbamate, 4,5 and 4,7-dichloroisatin, 6-chloroisatin, 7-chloroisatin, 6-chloroisatin-3-oxime, 5-chloroisatin-3-oxime, N(3-chlorophenyl) propionamide, 2-cyano-3-(2,4-dichlorophenyl) propenoic acid, 2,4,6-trichlorophenoxyacetic acid, N-(3-chlorophenyl)-1,2,3,6-tetrahydrophthalimide, N, N1-bis (3,4-dichlorobenzylidene)-3,4,-dichlorobenzylidene diamine, N-(3-chlorophenyl) pyruvamide, 1, 3-bis (3-chloro-4-methylphenyl) thiourea, N-(3-chlorophenyl) tribromoacetamide, ethyl a , b -dibromocinnamate, a -chloro-a  (2,4-dichlorophenyl) acetic acid, 2-benzothiazolyl N-(3-chlorophenyl) thiocarbamate, cinnamohydroxamic acid, ethyl naphtholate, n-heptaldehyde, N-(3 - chlorophenyl) - 4 - amino - 2 - hydroxybenzamide, 3-bromopropyl N-(4-bromophenyl) carbamate, phthalyl hydrazide, amalic acid, hydrocinnamic acid, 2-bromoethyl N-(4-bromophenyl) carbamate, a -hydrazoisobutyric acid dibenzoylmethane, N-(4-cholorophenyl) a -chloropropionamide, b -morpholino-p-bromopropiophenone hydrochloride, ethyl 3-(2,5-dichlorophenyl) carbazate, a -(4-chlorophenyl)-a -methyl-2-pyridinemethanol hydrochloride, N-phenylglycinonitrile, carboxymethyl-N, N-dimethyldithiocarbamate and tetrachlorophthalic acid.  Between 0.05 and 8 ounces of antagonistic agent may be used for each bushel of seed.  The antagonistic agent, e.g. mixed with a wetting agent, may be dispersed in an inert solid carrier such as talc, clay, calcium carbonate, diatomaceous earth or sawdust, or it may be dissolved or dispersed in a liquid such as kerosene, acetone, benzine, toluene, xylene and water.  Seeds specified are those of wheat, barley, oats, flax, sugar-beet, safflower, sunflower, rape, mustard and peas.  The seeds may be coated with a fungicide, insecticide and/or plant nutrient in addition to an antagonistic agent.  Specifications 862,194 and 894,614 are referred to.